Artificial resin and process of making the same.



BYRON IB. GOLDSMITH, OF NEW YORK, N. Y., ASSIGNOR TO REDMANOL-CHEMICAL PRODUCTS COMPANY, OF CHICAGO, ILLINOIS, A CORPORATION OF WEST VIB- GIN IA.

ARTIFICIAL RESIN AND PROCESS OF MAKING THE SAME.

No Drawing.

To all whom it may concern:

Be it known that I, BYRON B. GOLDSMITH, a cltizen of the United States, residing in the city, county, and State of New York,

to a process whereby the compounds in question may be produced.

I have discovered that, on heating together. hexamethylene tetramin and} either ordinary phenol (C H OH) cresol, or other phenols, a reaction takes place with the formation of useful products varying among themselves according to the particular phenol employed.

The compound from ordinary phenol (C l-LOH) is made by mixing phenol and hexamethylene-tetramin in a convenient vessel and heating the mixture, gradually ralsing the temperature. This is continued until a sam letaken from the vessel s0lidifies on coohng, when the mixture ispoured out and allowed to cool. The compound thus formed has an amber color and resembles resin in appearance. It may be powdered and ressed into convenient shapes when heated. It may, on the other hand, be dissolved in proper solvents, as for instance acetone, and may be used as a varnish. When subjected to heat and pressure in a mold, this compound becomes harder and more insoluble.

The heat required for causing the reaction to start need not be higher than the boiling point of 'water for some of the phenols. For others a high temperature is required, particularly if of solid form and used dry instead of in solution.

For instance, if ordinary phenol (3 H OH) is heated with hexamethylene-tetramin on the Water bath the two easily react, because phenol is liquid at the temperature of boiling Water.

The proportions in which the ingredients- Specification of Letters Patent.

- soluble in known solvents.

Patented June 19, 1917.

4 Application filed July 27, 1910. Serial No. 574,026.

are mixed will vary according to the particular phenol used, and the most suitable proportion for each phenol and for the particular end in View can readily be determined by experiment.

Good results may be obtained by mixing three or four parts by Weight of either true phenol or cresol with one part by weight of hexamethylenetetramin. Four parts by weight of the phenolic body to one part by weight of the methylene-amin body corresponds to about six mols of the phenolic body to one mol of the methylene-amin body. It will be noted that such proportions. furnish at leastsubstantially one phenolic group of the phenglic body to each methylene group of the active methylene body.

,These proportions are given as examples, as

I find that the proportions may vary within quite a wide range. As indicated above, the condensation product resembles resin, and is amorphous or non-crystalline. The re-action'is anhydrous, that is, there is no water formed in the re-action. On the other hand, ammonia is given off copiously durin proper solvents, when taken at the proper stage. When subjected to further heat treatment, however, the compound becomes harder and more insoluble, and in the final stage becomes infusible and practically in- It is a further advantage of the process that the materials may be readily measured in definite proportions, and that the proportion of the phenolic groups to the methylene groups may be maintained during the condensation process. Thus, there is no dilution due to the formation of water (none being formed) and there is no loss of methylene groups, as may be the case where formaldehyde is used. It is preferred to carry on the re-actions substantially in the absence of water.

so doing, I obviate the necessity of eliminating both the water of solution and'the water V water as an impurity, the percentage of water being so small, however, as to be negligible.

It is an economic advantage of my process that, during the reaction, ammoma is given off copiously and that this can be easily collected and used in preparing a fresh quantity of hexamethylene-tetramin. v The foregoing detailed description has been given for clearness of understanding, and no unnecessary limitation should be understood therefrom, but the appended claims should be construced as broadly as permissible in View of the prior art. An suitable hydroxy aromatic compound, suc as phenol or its homologues, and any suitable equivalent active methylene body may be employed as substitutes for the preferred materials mentioned.

What I claim is 1. A composition of matter of the character set forth, comprising the product of anhydrous reactio directly between hexamethylenetetramm and a hydroxy aromatic compound of the character set forth, subjected to the action of heat, the substances compounded in such proportions as to furnish at least substantially one phenolic group of the hydroxy aromatic compound to each methylene group of the hexamethylenetetramin.

2. An amorphous composition of matter having qualities of the character set forth and containing nitrogen and produced by direct anhydrous combining of hexamethylenetetramin and a phenolic body of the I character set forth, substantially in the absence of water, employing such proportions as to furnish at least substantially one phenolic group .to each methylene group.

3. An anhydrous process of producing a condensation product, which consists in producing an anhydrous reaction, substantially in the absence of water, in a mixture which includes an active methylene body and a phenolic body, employing such proportions and such application of heatas to produce a non-crystalline condensation product,

4. An anhydrous process of producing a condensation product, which consistsin roducmg an anhydrous reaction, substantially 1nthe absence of water, in a mixture which includes a phenolic body and hexamethylenetetramin, employing such proportions and such conditions of treatment, including the application of heat, as to produce a fusible non-crystalline condensation-product.

" 5. An anhydrous process of producing a condensation product, which consists in producing an anhydrous reaction, substantially in the absence of water, in a mixture which includes a phenolic body and a methyleneamin body which normally exists as a solid, employing such proportions and such conditions of treatment, including such application of heat, as to produce a final amorphous, infusible condensation product.

6. An anhydrous process of producing a condensation product, which consists in heating a mixture which comprises a phenolic body and hexamethylenetetramin, substantially free from water, employing such proportions and such application of heat as to produce a non-crystalline condensation product.

7. An anhydrous process of producing a fusible condensation product, which conslsts in producing an anhydrous reaction, substantially in the absence of water, in a mixture Which includes a phenolic body and an active methylene body which normally exists, as a solid, employing such proportions and such application of heat as to produce a fusible, non-crystalline condensation product,and introducing a solvent as one step in the process.

8. An anhydrous process of producing a condensation product, which consists in producing an anhydrous reaction, substantially in the absence of water, in a mixture which comprises a hydroxy-aromatic compound of the character set forth and a methylene body of the character set forth, compounded insuch proportions as to furnish approximately one methylene group to each phenol group, employing'such heat treatment as to elimlnate a large percentage of nitrogen in the form of a nitrogen compound formed during the reactionand produce a non-cryst/alline condensation product.

9. An anhydrous process of producing a condensation product, which consists in producing an anhydrous reaction, substantially in the absence ofwater, in a mixture which comprises a phenol and hexamethyleneteheat treatment as to produce said non-crystalline condensation product.

11. An amorphous composition of matter,

comprising the product of anhydrcusreaction substantially in the absence of water in a mixture comprising a phenolic body of the character set forth and a methyleneamin body, taken in such proportions and subjected to such heat treatment as to produce a final infusible product.

7 12. A composition of matter comprising he product of anhydrous reaction under the application of heat and substantially in the absence of water, in a mixture comprising a phenol and hexamethlyenetetramin, taken in such proportions and subjected to such heat treatment as to produce a non-crystalline condensation product.

13. A non-crystalline condensation product, comprising the product of anhydrous reaction under the application of'heat and substantially in the absence of water, in a m1xture comprising a phenolic body of the character set forth and hexamethylenetetramin, taken in such proportions as to afford at least substantially one phenolic group to each methylene group.

14-. A process of producing a condensatlon product, which consists in producing an anhydrous reaction in the absence of a catalyzer between a methylene-aminbody and a phenolic body with the evolution of ammonia, employing such proportions and such application of heat as to produce a noncrystalline condensation product.

15. A process of producing a condensatlon product, which consists in producing an anhydrous reaction in the absence of a catalyz'er between a methylene-amin body and a phenolic body with the evolution of ammonia, employing such proportions as to afford at least substantially one methylene group to one phenolic group and such application of heat as to produce a non-crystalline condensatlon product.

16. A process of producing a condensation product which consists in producing an anhydrous reaction in the absence of a catalyzer between hexamethylenetetramin and a. phenolic body with the evolution of ammonia, employing such proportions and such application of heat as to produce anoncrystallinc condensation product.

17. A process of producing a condensation product. which consists in producing an anhydrous re-action in the absenceof a catalyzer between hexamethylenetetramin and a phenolic body with the evolution of ammonia. employing such proportions as to afford at least substantially one methylene group to one phenolic group and such application of heat as to produce a non-crystalline condensatiou product.

18. A non-crystalline condensation product of the character set forth, comprising the product of anhydrous reaction, with evolution of ammonia. in a mixture comprising a phenolic body of the cha acter set forth and a metl'iylene-amin body, taken in such pro 'mrtions and subjected to such heattreatment in the absence of a catalytic agent as to produce said non-crystalline condensation product.

19. A non-crystalline condensation product of the character set forth, comprising the product of anhydrous reaction, with evolution of ammonia. in a mixture comprising a phenolic body of the character set forth, and heXan'iethylenetetramin taken in such proportions and subjected to such heat treatment in the absence of a catalytic agent as to produce said non-crystalline condensation product.

BYRON B. GOLDSMITH.

Witnesses 2 C. E. FINN, V. H. KULKA. 

